Abstract
An efficient, one-pot quantitative procedure for the preparation of benzo[a]pyrano[2,3-c]phenazine derivatives from four-component condensation reaction of 2-hydroxynaphthalene-1,4-dione, benzene-1,2-diamine, aromatic aldehydes, and malononitrile in the presence of [(EtO)3Si(CH2)3N+H3][CH3COO−] as basic ionic liquid as catalyst in homogenous solution under solvent-free conditions at 90 °C is described. Simple procedure, high yields, short reaction times, and an environmentally benign method are advantages of this protocol. The [(EtO)3Si(CH2)3N+H3][CH3COO−] can be recovered and reused several times without loss of its activity.
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The data that support the findings of this study are available in the supplementary material of this article.
References
Calvo-Flores, F.G.: Sustainable chemistry metrics. Chemsuschem 2, 905–919 (2009). https://doi.org/10.1002/cssc.200900128
Wakai, C., Oleinikova, A., Weingärtner, H.: Reply to “Comment on ‘how polar are ionic liquids? determination of the static dielectric constant of an imidazolium-based ionic liquid by microwave spectroscopy.’” J. Phys. Chem. B 110, 5824 (2006). https://doi.org/10.1021/jp0601973
Chen, Y., Han, X., Liu, Z., Li, Y., Sun, H., Wang, H., Wang, J.: Thermal decomposition and volatility of ionic liquids: factors, evaluation and strategies. J. Mol. Liq. 366, 120336 (2022). https://doi.org/10.1016/j.molliq.2022.120336
Ghorbani, M., Simone, M.I.: Develo** new inexpensive room-temperature ionic liquids with high thermal stability and a greener synthetic profile. ACS Omega 5, 12637–12648 (2020). https://doi.org/10.1021/acsomega.9b04091
Niedermaier, I., Kolbeck, C., Taccardi, N., Schulz, P.S., Li, J., Drewello, T., Wasserscheid, P., Steinrück, H.P., Maier, F.: Organic reactions in ionic liquids studied by in situ XPS. ChemPhysChem 13, 1725–1735 (2012). https://doi.org/10.1002/cphc.201100965
Gao, Y., Arritt, S.W., Twamley, B., Shreeve, J.M.: Guanidinium-based ionic liquids. Inorg. Chem.. Chem. 44, 1704–1712 (2005). https://doi.org/10.1021/ic048513k
Kirchhecker, S., Esposito, D.: Amino acid based ionic liquids: a green and sustainable perspective. Curr. Opin. Green Sustain. Chem. 2, 28–33 (2016). https://doi.org/10.1016/j.cogsc.2016.09.001
Yunus, N.M., Mutalib, M.I.A., Man, Z., Bustam, M.A., Murugesan, T.: Solubility of CO2 in pyridinium based ionic liquids. Chem. Eng. J. 189–190, 94–100 (2012). https://doi.org/10.1016/j.cej.2012.02.033
Chen, X., Liu, G., Yuan, S., Asumana, C., Wang, W., Yu, G.: Extractive desulfurization of fuel oils with thiazolium-based ionic liquids. Sep. Sci. Technol. 47, 819–826 (2012). https://doi.org/10.1080/01496395.2011.637281
Fredlake, C.P., Crosthwaite, J.M., Hert, D.G., Aki, S.N.V.K., Brennecke, J.F.: Thermophysical properties of imidazolium-based ionic liquids. J. Chem. Eng. Data 49, 954–964 (2004). https://doi.org/10.1021/je034261a
Sanghi, S., Willett, E., Versek, C., Tuominen, M., Coughlin, E.B.: Physicochemical properties of 1,2,3-triazolium ionic liquids. RSC Adv. 2, 848–853 (2012). https://doi.org/10.1039/c1ra00286d
Greaves, T.L., Drummond, C.J.: ChemInform abstract: protic ionic liquids: properties and applications. ChemInform 39, 206–237 (2008). https://doi.org/10.1002/chin.200818249
Bienaymé, H., Hulme, C., Oddon, G., Schmitt, P.: Maximizing synthetic efficiency: multi-component transformations lead the way. Chem. A Eur. J. 6, 3321–3329 (2000). https://doi.org/10.1002/1521-3765(20000915)6:18%3c3321::AID-CHEM3321%3e3.0.CO;2-A
Laursen, J.B., Nielsen, J.: Phenazine natural products: biosynthesis, synthetic analogues, and biological activity. Chem. Rev. 104, 1663–1685 (2004). https://doi.org/10.1021/cr020473j
Borrero, N.V., Bai, F., Perez, C., Duong, B.Q., Rocca, J.R., **, S., Huigens, R.W.: Phenazine antibiotic inspired discovery of potent bromophenazine antibacterial agents against Staphylococcus aureus and Staphylococcus epidermidis. Org. Biomol. Chem.Biomol. Chem. 12, 881–886 (2014). https://doi.org/10.1039/c3ob42416b
Hu, L., Chen, X., Han, L., Zhao, L., Miao, C., Huang, X., Chen, Y., Li, P., Li, Y.: Two new phenazine metabolites with antimicrobial activities from soil-derived Streptomyces species. J. Antibiot.Antibiot. 72, 574–577 (2019). https://doi.org/10.1038/s41429-019-0163-2
Verma, K., Tailor, Y.K., Khandelwal, S., Agarwal, M., Rushell, E., Kumari, Y., Awasthi, K., Kumar, M.: An efficient and environmentally sustainable domino protocol for the synthesis of structurally diverse spiroannulated pyrimidophenazines using erbium doped TiO2 nanoparticles as a recyclable and reusable heterogeneous acid catalyst. RSC Adv. 8, 30430–30440 (2018). https://doi.org/10.1039/c8ra04919j
Guttenberger, N., Blankenfeldt, W., Breinbauer, R.: Recent developments in the isolation, biological function, biosynthesis, and synthesis of phenazine natural products. Bioorg. Med. Chem.. Med. Chem. 25, 6149–6166 (2017). https://doi.org/10.1016/j.bmc.2017.01.002
Low, Z.Y., Yip, A.J.W., Lal, S.K.: Repositioning ivermectin for covid-19 treatment: molecular mechanisms of action against SARS-CoV-2 replication. Biochim. Biophys. Acta Mol. Basis Dis. 1868, 166294 (2022). https://doi.org/10.1016/j.bbadis.2021.166294
Rhee, H.K., Yoo, J.H., Lee, E., Kwon, Y.J., Seo, H.R., Lee, Y.S., Choo, H.Y.P.: Synthesis and cytotoxicity of 2-phenylquinazolin-4(3H)-one derivatives. Eur. J. Med. Chem. 46, 3900–3908 (2011). https://doi.org/10.1016/j.ejmech.2011.05.061
Le-Nhat-Thuy, G., Dang Thi, T.A., Nguyen Thi, Q.G., Hoang Thi, P., Nguyen, T.A., Nguyen, H.T., Nguyen Thi, T.H., Nguyen, H.S., Nguyen, T.: Van: synthesis and biological evaluation of novel benzo[a]pyridazino[3,4-c]phenazine derivatives. Bioorg. Med. Chem. Lett.. Med. Chem. Lett. 43, 128054 (2021). https://doi.org/10.1016/j.bmcl.2021.128054
Shirzaei, F., Shaterian, H.R.: [(EtO)3Si(CH2)3NH3+][CH3COO−] as a novel basic ionic liquid catalyzed green synthesis of new 2-(phenylsulfonyl)-1H-benzo[a]pyrano[2,3-c]phenazin-3-amine derivatives. J. Mol. Struct.Struct. 1256, 132558 (2022). https://doi.org/10.1016/j.molstruc.2022.132558
Shirzaei, F., Shaterian, H.R.: Basic ionic liquid, 2-hydroxyethylammonium formate, catalyzed one-pot synthesis of novel 2-(phenylsulfonyl)-1H-benzo[a]pyrano[2,3-c]phenazin-3-amine derivatives. Res. Chem. Intermed.Intermed. 48, 751–770 (2022). https://doi.org/10.1007/s11164-021-04627-z
Shaterian, H.R., Moradi, F., Mohammadnia, M.: Nano copper(II) oxide catalyzed four-component synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives. Comptes Rendus Chim. 15, 1055–1059 (2012). https://doi.org/10.1016/j.crci.2012.09.012
Shaterian, H.R., Mohammadnia, M.: Mild basic ionic liquid catalyzed four component synthesis of functionalized benzo[a]pyrano[2,3-c]phenazine derivatives. J. Mol. Liq. 177, 162–166 (2013). https://doi.org/10.1016/j.molliq.2012.11.006
Shaabani, A., Ghadari, R., Arabieh, M.: Synthesis of a new library of pyrano-phenazine derivatives via a novel three-component protocol. Helv. Chim. Acta. Chim. Acta 97, 228–236 (2014). https://doi.org/10.1002/hlca.201300006
Tabibian, M., Mohebat, R., Tabatabaee, M.: A novel one-pot and rapid synthesis of polyfunctionalized benzo[a]pyrimido[5′,4′:5,6]pyrido[2,3-c]phenazine derivatives under microwave irradiation. Turkish J. Chem. 42, 1008–1017 (2018). https://doi.org/10.3906/kim-1710-13
Naeimi, H., Zarabi, M.F.: Multisulfonate hyperbranched polyglycerol functionalized graphene oxide as an efficient reusable catalyst for green synthesis of benzo[a]pyrano-[2,3-c]phenazines under solvent-free conditions. RSC Adv. 9, 7400–7410 (2019). https://doi.org/10.1039/C8RA10180A
Hasaninejad, A., Firoozi, S.: One-pot, sequential four-component synthesis of benzo[c]pyrano[3,2-a]phenazine, bis-benzo[c]pyrano[3,2-a]phenazine and oxospiro benzo[c]pyrano[3,2-a]phenazine derivatives using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an efficient and reusable solid bas. Mol. Divers. 17, 499–513 (2013). https://doi.org/10.1007/s11030-013-9446-x
Yazdani-elah-abadi, A., Razeghi, M., Shams, N.: Fulvic acid: an efficient and green catalyst for the one-pot four-component domino synthesis of benzo[a]phenazine annulated heterocycles in aqueous medium. Org. Prep. Proced. Int.Proced. Int. 52, 48–55 (2020). https://doi.org/10.1080/00304948.2019.1697608
Marsh, K.N., Boxall, J.A., Lichtenthaler, R.: Room temperature ionic liquids and their mixtures—a review. Fluid Phase Equilib.Equilib. 219, 93–98 (2004). https://doi.org/10.1016/j.fluid.2004.02.003
Dashteh, M., Safaiee, M., Baghery, S., Zolfigol, M.A.: Application of cobalt phthalocyanine as a nanostructured catalyst in the synthesis of biological henna-based compounds. Appl. Organomet. Chem.Organomet. Chem. 33, 1–14 (2019). https://doi.org/10.1002/aoc.4690
Safaei-Ghomi, J., Kareem Abbas, A., Shahpiri, M.: Synthesis of imidazoles promoted by H3PW12O40-amino-functionalized CdFe12O19@SiO2 nanocomposite. Nanocomposites 6, 149–157 (2020). https://doi.org/10.1080/20550324.2020.1858246
Ghorbani, A., Masoud, C., Lotfi, M.: Synthesis and characterization of spinel FeAl2O4 (hercynite) magnetic nanoparticles and their application in multicomponent reactions. Res. Chem. Intermed.Intermed. 4, 5705–5723 (2019). https://doi.org/10.1007/s11164-019-03930-0
Nikoorazm, M., Khanmoradi, M.: Application of Cu(II)-Guanine complexes anchored on SBA-15 and MCM-41 as efficient nanocatalysts for one-pot, four-component domino synthesis of phenazine derivatives and investigation of their antimicrobial behavior. Catal. Lett.. Lett. 150, 2823–2840 (2020). https://doi.org/10.1007/s10562-020-03185-0
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We are thankful to the University of Sistan and Baluchestan Research Council for the partial support of this research.
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Shirzaei, F., Shaterian, H.R. [(EtO)3Si(CH2)3N+H3][CH3COO−] as Basic Ionic Liquid Catalyst Promoted Green Synthesis of Benzo[a]pyrano[2,3-c]phenazine Derivatives in Homogenous Solution. J Solution Chem 53, 328–340 (2024). https://doi.org/10.1007/s10953-023-01332-w
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DOI: https://doi.org/10.1007/s10953-023-01332-w